Benzonitrile → HCID 53389669, compound

HRID 1020861Notes

Reaction equation

HRID 1020861 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[C:5](\[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)/[CH3:6].[C:18](#[N:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:4]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:25][N:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=2)[C:5]=1[CH3:6])=[O:17]

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 67448671HCID 67448671, compound

Product 1

HCID 53389669HCID 53389669, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

According to AVV A, (Z-3-(4-ethoxyphenylamino)-but-2-enoic acid methylester (235.3 mg, 1.0 mmol, 1.0 equiv.) was stirred with Cu(OAc)2 (544.9 mg, 3.0 mmol, 3.0 equiv.) into benzonitrile (3.0 ml, 29.4 mmol, 29.4 equiv.) for 14 hours at 120° C. The olive-green oily raw product (490.3 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 95:5→0:100). The desired product was obtained in the form of a white solid (291.0 mg, 0.87 mmol, 87%).

Workup

  1. customThe olive-green oily raw product (490.3 mg) was purified by means of column chromatography (silica gel (50 g), pentane/EtOAc 95:5→0:100)

Sources & evidence

ORD record
ord-d1099f58bd2f4ab3bbde707125c90be2
Source dataset
uspto-grants-2014_05
Patent number
US08716485B2

Reaction notes

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